In Shakespearean drama, the conception of acting as “play” was shaped by an inheritance of medieval “player” routines and strategies and by the environment of the professional Elizabethan theater. Arguing from a theoretical and practical discussion of the role of “play” in medieval drama, using the example of Mankind, this essay examines how the actor, seen as engaged in both collaborative and competitive play, can illuminate certain strategies in Shakespeare's work. Examples drawn from Richard III, Twelfth Night, Much Ado about Nothing, and King Lear illustrate how different kinds of playerly routines register the actor's dramatic situation on stage and how these scenes are deployed for the poetic and dramatic ends of the works. These deployments register a distinctly premodern approach to the energies of the theatrical occasion, an approach that is submerged by later developments.